The Red Sox were in it until the bitter end, but free agent starter Jon Lester ultimately decided to join the Chicago Cubs on Wednesday morning. The 30-year old accepted Chicago’s offer of 6 years, $155M, and officially bought into Theo Epstein’s vision for the future of the Cubs. As Chicago celebrates winning the Lester sweepstakes, the Red Sox now find themselves looking for a new ace to plant atop their rotation. On the free agent market there aren’t many sound options outside of right handers Max Scherzer and James Shields. While Boston probably won’t get involved in Scherzer’s market, the team could look at bringing in Shields for a more favorable deal. The 33-year old starter spent last season heading the Kansas City Royals rotation, and posted a 3.21 ERA in 32 games started. For the eighth straight season, Shields stuck to his reputation as an innings eater and posted another 200-plus innings campaign. However, the wheels fell off Shields otherwise solid season during the playoffs, as the starter posted an ERA over 6.00 in five postseason starts. Shields isn’t the teams only option though, the club can also use their arsenal of trade chips to reel in an ace on the trade front. With Jeff Samardzija now off the board, Boston can look towards pitchers like Cincinnati Reds’ right handers Johnny Cueto and Mat Latos. While the price tag on Cueto remains remarkably high for a pitcher entering his contract season, it’s important to not forget that the 28-year old is coming off a season in which he finished as the National League Cy Young runner up behind Clayton Kershaw. Latos, however, figures to command a more realistic package from Boston, after a successful yet injury prone season. Despite only starting 16 games, the 26-year old finished the season with an ERA of 3.25 and a 1.15 WHIP. When healthy, Latos can be an extremely valuable asset to a starting rotation, and has the potential to accumulate a ton of innings if need be. With Lester now out of the picture, you can bet that we’ll hear Cueto or Latos connected to Boston before the offseason is over.

Although the team lost out on their prized possession of the offseason, General Manager Ben Cherington is still confident that he can assemble a formidable starting staff. In his third year at the helm for the Red Sox, Cherington admitted that it’s not a matter of if the team acquires pitching it’s when. Cherington was quick to not put a timeline on his search for staring arms, and instead preach an opportunistic approach to rebuilding the rotation. (Ben Cherington on Red Sox’ rotation outlook: “We’ll be able to put together a good pitching staff”)

Since the start of the offseason, the most popular fallback option to Jon Lester has been Philadelphia Phillies left-hander Cole Hamels. Now that Lester is officially off the board for the Red Sox, the team can look deeper into possibly acquiring the southpaw. However, according to Phillies manager Ryne Sandberg, his club would have to be ‘wowed’ by a package in exchange for their ace. Reportedly, the Phillies are very high on Red Sox second baseman turned outfielder Mookie Betts, and have scouted Boston’s farm system extensively. (If Red Sox land Cole Hamels, it may be costly)

Shortly after Ben Cherington told the media that the team is not close on acquiring a pitcher, news broke that Boston could be zeroing in on a trade with the Arizona Diamondbacks. The potential deal would send left-handed starter Wade Miley to Boston in exchange for some minor league pieces. Miley, who just turned 28 years old, projects as a middle-to-back end arm in Boston’s rotation. The former first round draft pick is arbitration eligible for the first time this winter, and won’t hit free agency until 2018. (Red Sox possibly “close” to Wade Miley trade with Diamondbacks)

Tweet of the day: Give ’em hell in Chicago, Jon!

To Red Sox Nation, I understand the disappointment. Boston will always have a big place in my heart and we'll always consider y'all family!